1-(2-methylbutanone)-3-prenylphloroglucinol | 71539-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methylbutanone)-3-prenylphloroglucinol
• 英文别名: 2-methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)butan-1-one；2-Methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one；2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]butan-1-one
• CAS: 71539-60-1
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: KYHKDOKSARWIDI-UHFFFAOYSA-N

物化性质

• 沸点：
  421.4±45.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-methylbutanone)-3-prenylphloroglucinol 在 iron(III) chloride adsorbed on silica gel 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 以51%的产率得到2-Methyl-1-[1,3,7,9-tetrahydroxy-6-(2-methylbutanoyl)-4,8-bis(3-methylbut-2-enyl)dibenzofuran-2-yl]butan-1-one
  参考文献：
  名称：

  通过催化碳插入甲酰基CH键中形成不同的烷酮。方便地获得天然的Achyrofuran

  摘要：

  一个多世纪前，重氮甲烷与醛的首次反应生成了甲基酮。在此期间，醛很少与三甲基甲硅烷基重氮甲烷，重氮乙酸酯和芳基重氮甲烷发生同系化反应。这项工作描述了一种由不稳定的重氮烷烃聚合酮组装的温和方法，包括使用双取代（内部）亲核试剂进行手性酮合成的实例。该方法对空间拥挤具有显着的耐受性，这是通过对复杂的二苯并呋喃呋喃呋喃进行的简单处理得到证实的。

  DOI：

  10.1021/ol9010932
• 作为产物：
  描述：

  2-methyl-1-(2,4,6-trimethoxy-3-(3-methylbut-2-enyl)phenyl)butan-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到1-(2-methylbutanone)-3-prenylphloroglucinol
  参考文献：
  名称：

  通过催化碳插入甲酰基CH键中形成不同的烷酮。方便地获得天然的Achyrofuran

  摘要：

  一个多世纪前，重氮甲烷与醛的首次反应生成了甲基酮。在此期间，醛很少与三甲基甲硅烷基重氮甲烷，重氮乙酸酯和芳基重氮甲烷发生同系化反应。这项工作描述了一种由不稳定的重氮烷烃聚合酮组装的温和方法，包括使用双取代（内部）亲核试剂进行手性酮合成的实例。该方法对空间拥挤具有显着的耐受性，这是通过对复杂的二苯并呋喃呋喃呋喃进行的简单处理得到证实的。

  DOI：

  10.1021/ol9010932

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops
  作者：Yusuke Tsurumaru、Kanako Sasaki、Tatsuya Miyawaki、Yoshihiro Uto、Takayuki Momma、Naoyuki Umemoto、Masaki Momose、Kazufumi Yazaki

  DOI：10.1016/j.bbrc.2011.11.125

  日期：2012.1

  HlPT-1 catalyzed the first transfer of dimethylallyl moiety to phloroglucinol derivatives, phlorisovalerophenone, phlorisobutyrophenone and phlormethylbutanophenone, leading to the formation of humulone and lupulone derivatives. HlPT-1 also recognized naringenin chalcone as a flavonoid substrate to yield xanthohumol, and this broad substrate specificity is a unique character of HlPT-1 that is not seen in

  蛇麻草的雌花（Humulus lupulus L.）发育出大量的称为毛豆蛋白腺的毛状毛，其中包含多种prenylated化合物，例如α-酸和β-酸（分别为humulone和lupulone）以及黄腐酚（chanthohumol），查尔酮衍生物。这些异戊二烯基化的化合物通过异戊二烯基转移酶生物合成，所述异戊二烯基转移酶催化二甲基烯丙基部分向芳族物质的转移。在我们以前的工作中，我们在从富含卢普林的花组织构建的cDNA文库中发现HlPT-1是此类异戊二烯基转移酶的候选基因。在这项研究中，我们使用杆状病毒感染的昆虫细胞中表达的重组蛋白表征了HlPT-1的酶学性质。HlPT-1催化了二甲基烯丙基部分向间苯三酚衍生物苯并异戊二酮的首次转移，苯并异丁苯酮和苯并甲基丁苯酮，导致形成hu草酮和卢普隆衍生物。HlPT-1还认为柚皮素查尔酮为类黄酮底物，可产生黄腐酚，这种广泛的底物特异性是HlPT-1的独特特征
• A Heteromeric Membrane-Bound Prenyltransferase Complex from Hop Catalyzes Three Sequential Aromatic Prenylations in the Bitter Acid Pathway
  作者：Haoxun Li、Zhaonan Ban、Hao Qin、Liya Ma、Andrew J. King、Guodong Wang

  DOI：10.1104/pp.114.253682

  日期：2015.3

  Bitter acids (α and β types) account for more than 30% of the fresh weight of hop (Humulus lupulus) glandular trichomes and are well known for their contribution to the bitter taste of beer. These multiprenylated chemicals also show diverse biological activities, some of which have potential benefits to human health. The bitter acid biosynthetic pathway has been investigated extensively, and the genes for the early steps of bitter acid synthesis have been cloned and functionally characterized. However, little is known about the enzyme(s) that catalyze three sequential prenylation steps in the β-bitter acid pathway. Here, we employed a yeast (Saccharomyces cerevisiae) system for the functional identification of aromatic prenyltransferase (PT) genes. Two PT genes (HlPT1L and HlPT2) obtained from a hop trichome-specific complementary DNA library were functionally characterized using this yeast system. Coexpression of codon-optimized PT1L and PT2 in yeast, together with upstream genes, led to the production of bitter acids, but no bitter acids were detected when either of the PT genes was expressed by itself. Stepwise mutation of the aspartate-rich motifs in PT1L and PT2 further revealed the prenylation sequence of these two enzymes in β-bitter acid biosynthesis: PT1L catalyzed only the first prenylation step, and PT2 catalyzed the two subsequent prenylation steps. A metabolon formed through interactions between PT1L and PT2 was demonstrated using a yeast two-hybrid system, reciprocal coimmunoprecipitation, and in vitro biochemical assays. These results provide direct evidence of the involvement of a functional metabolon of membrane-bound prenyltransferases in bitter acid biosynthesis in hop.

  苦酸（α和β型）占啤酒花腺毛重量的30%以上，是啤酒苦味的来源。这些多烯基化合物的生物活性多种多样，其中一些可能对人体健康有益。苦酸的生物合成途径已经过广泛研究，苦酸合成早期步骤的基因也已克隆并确定功能。然而，人们对催化β-苦酸合成途径中三个连续烯基化步骤的酶知之甚少。在此，我们采用酵母（酿酒酵母）系统对芳香烯基转移酶（PT）基因的功能进行了鉴定。利用酵母系统对从啤酒花腺毛特异性互补DNA文库中获得的两个PT基因（HlPT1L和HlPT2）进行了功能鉴定。在酵母中，经过密码子优化的PT1L和PT2与上游基因共表达可产生苦酸，但单独表达任一PT基因时均未检测到苦酸。PT1L和PT2中富含天冬氨酸的基序的逐步突变进一步揭示了β-苦酸生物合成中这两种酶的烯基化序列：PT1L仅催化第一个烯基化步骤，PT2催化随后的两个烯基化步骤。利用酵母双杂交系统、相互共沉淀和体外生化分析，证明了PT1L和PT2之间的相互作用形成的代谢体。这些结果直接证明了膜结合烯基转移酶的功能代谢体参与啤酒花苦酸生物合成。
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C−H Bond. Concise Access to the Natural Precursor of Achyrofuran
  作者：Andrew J. Wommack、David C. Moebius、Austin L. Travis、Jason S. Kingsbury

  DOI：10.1021/ol9010932

  日期：2009.8.6

  Over a century ago, the first reactions of diazomethane with aldehydes delivered methyl ketones. In the interim, aldehydes have been homologated with trimethylsilyldiazomethane, diazoacetates, and aryldiazomethanes, on rare occasion with catalysis. This work describes a mild procedure for convergent ketone assembly from nonstabilized diazoalkanes, including examples of chiral ketone synthesis with

  一个多世纪前，重氮甲烷与醛的首次反应生成了甲基酮。在此期间，醛很少与三甲基甲硅烷基重氮甲烷，重氮乙酸酯和芳基重氮甲烷发生同系化反应。这项工作描述了一种由不稳定的重氮烷烃聚合酮组装的温和方法，包括使用双取代（内部）亲核试剂进行手性酮合成的实例。该方法对空间拥挤具有显着的耐受性，这是通过对复杂的二苯并呋喃呋喃呋喃进行的简单处理得到证实的。